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Citation: ZHAO Hua-Rong, WU Bai-Le, LI Xiu-Ling, QIN Min-Rui, CAI Huang-Ju. Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment[J]. University Chemistry, ;2016, 31(8): 76-80. doi: 10.3866/PKU.DXHX201511014 shu

Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment

Department of Chemistry, Zhejiang University, Hangzhou 310058, P. R. China

An advanced chemistry experiment involving organic synthesis and chemical analysis is proposed. This experiment is suitable for both chemistry major and non-chemistry major students. ciscyclohex-4-ene-1,2-dicarboxylic acid can be prepared by Diels-Alder reaction with 1,3-butadiene generated readily in situ by means of chelotropic extrusion of sulfur dioxide from 2,5-dihydrothiophene-1,1-dioxide. The Diels-Alder adduct formed in this instance is readily hydrolysed to the dicarboxylic acid by heating with water. The purity of product is analyzed using acid-base titration, and the structure of product is characterized by M.P., IR and ¹H NMR.
- Diels-Alder reaction,
- cis-Cyclohex-4-ene-1,2-dicarboxylic acid,
- Synthesis,
- Purity analysis
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